335452

Lithium (trimethylsilyl)acetylide solution

0.5 M in THF

• Synonym(s): (Trimethylsilyl)ethynyllithium
• Linear Formula: (CH₃)₃SiC≡CLi
• CAS Number: 54655-07-1
• Molecular Weight: 104.15
• Beilstein: 3587411
• MDL number: MFCD00075059
• UNSPSC Code: 12352103
• PubChem Substance ID: 24860321
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• concentration: 0.5 M in THF
• density: 0.88 g/mL at 25 °C
• SMILES string: [Li]C#C[Si](C)(C)C
• InChI: 1S/C5H9Si.Li/c1-5-6(2,3)4;/h2-4H3;
• InChI key: ZVXXEONXFWSCIZ-UHFFFAOYSA-N

Description

Application

Lithium (trimethylsilyl)acetylide can be used as a reagent:

• In the transmetalation and nucleophilic displacement reactions.[1]
• To prepare propargylic alcohol derivatives by reacting with aldehydes and ketones.[1]
• To synthesize α,βynones by treating with Weinreb amide or with isoxazolidide.[1]
• Along with Grignard reagent to convert γ- and δ-thiolactams to thioiminium salts, which are employed as key intermediates to produce disubstituted pyrrolidines.[2]

Reacts with halotriazines to produce conductive, anisotropic carbon-nitrogen materials.[3]

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H302,H314,H335,H336,H351
• Precautionary Statements: P210 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
• Target Organs: Respiratory system
• Supplementary Hazards: EUH019
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): -9.4 °F - closed cup
• Flash Point(C): -23 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves